132617-15-3

Basic information

• Product Name: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate
• Synonyms: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate
• CAS NO: 132617-15-3
• Molecular Weight: 156.181
• Mol File: 132617-15-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(132617-15-3)
• EPA Substance Registry System: (1R,4S)-4-hydroxycyclohex-2-en-1-yl acetate(132617-15-3)

Safety Data

• Hazardous Substances Data: 132617-15-3(Hazardous Substances Data)

Upstream product

• 6705-51-7 3,4-epoxycyclohexene 
• 75-36-5 acetyl chloride 
• 142-71-2 copper diacetate 
• 78776-45-1 cis-2-cyclohexenyl-1,4-diacetate 
• 121573-17-9 (3aR,7aS)-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 74293-60-0 (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 697741-23-4 (1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 942514-50-3 (1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-enol 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 1165952-91-9 cyclohexa-1,3-diene 
• 53762-85-9 (1S,4R)-Cyclohex-2-ene-1,4-diol 
• 108-24-7 acetic anhydride 
• 91923-19-2 1-acetoxy-4-trifluoroacetoxy-2-cyclohexene 
• 91923-19-2 trans-4-acetoxy-1-trifluoroacetoxy-cyclohex-2-ene 

Downstream Products

• 4908-50-3 (+/-)-3-(2-nitropropan-2-yl)cyclohexanone 
• 106251-94-9 3-(1-nitro-1-cyclohexyl)cyclohexanone 
• 50557-37-4 4-(acetoxy)cyclohex-2-enone 
• 94597-61-2 (S)-(-)-4-isopropenyl-2-cyclohexen-1-one 
• 930-68-7 cyclohexenone 
• 132513-03-2 (S)-4-benzoyloxycyclohex-2-enone 

Relevant articles and documents

Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams

A simple and mild process was developed for the highly stereoselective synthesis of halogenated bicyclic [4.3.0] and [3.3.0] γ-lactams, possessing four stereocenters, from easily available cyclic 2-enynamides. The reaction required only an inexpensive iron(II) halide under dry air and was tolerant of aryl, heteroaryl, and alkyl groups at the alkyne terminus.

The thio-adduct facilitated, enzymatic kinetic resolution of 4-hydroxycyclopentenone and 4-hydroxycyclohexenone

The addition of 3,4-dimethoxybenzyl thiol 8, as a benzyl thiol surrogate, to racemic 4-hydroxycyclopent-2-enone 2 and 4-hydroxycyclohex-2-enone 15 gave the corresponding cis-adducts (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclopentanone 4b and (±)-3-(3,4-dimethoxybenzylthio)-4- hydroxycyclohexanone 16 with good diastereocontrol. In both cases, subsequent treatment with vinyl acetate, in the presence of a lipase enabled enantiomer resolution. Thus, (+)-16 and the acetate of its enantiomer, (-)-(1R,2S)-2-(3,4- dimethoxybenzylthio)-4-oxocyclohexyl acetate, (-)-17 were isolated in 98% enantiomeric excess. Based on the 1,4-dioxygenation pattern, (-)-17 can be used to prepare both enantiomers of 4-(tert-butyldimethylsilyloxy)cyclohex-2-enone 19. Firstly, saponification, with a sub-stoichiometric amount of NaOMe, followed by a one-pot silyl ether formation-sulfide elimination sequence gave (+)-19. Then using the same starting material a 6-step sequence, featuring a diastereoselective NaBH4 reduction and a Cope-type sulfoxide elimination, gave (-)-19.

Enantioselective synthesis of (R)- and (S)-4-benzyloxy-2-cyclohexen-1-one

-